A glimpse into Gumroad’s work culture

Prior to the pandemic lockdown, Gumroad founder and Rolling Fund manager Sahil Lavingia mentioned he had relocated to the Portland area. Which, in my mind, immediately made Gumroad — an already interesting player in the creator community — an even more important startup for me to start tracking. Today, he posted about the work culture at Gumroad, which provides some valuable insights — and potentially inspiration — for folks who may be rethinking their work environments.

Today, working at Gumroad resembles working on an open source project like Rails. Except it’s neither open source, nor unpaid.

Instead of having meetings, people “talk” to each other via GitHub, Notion, and (occasionally) Slack, expecting responses within 24 hours. Because there are no standups or “syncs” and some projects can involve expensive feedback loops to collaborate, working this way requires clear and thoughtful communication.

Everyone writes well, and writes a lot.

Want more insights? Read “No meetings, no deadlines, no full-time employees.”


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